164

Caroline County MD Homes for Sale

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  • /29

    $750,000

    • 3 Beds
    • 2 Baths
    • 4,580 Sq Ft

    14236 Drapers Mill Rd, Greensboro, MD 21639

    STOP, LOOK, and READ...this may be exactly the property you’ve been searching for!! RESIDENTIAL / COMMERCIAL OPPORTUNITY – Zoned C-2, this versatile multi-use property offers endless possibilities! Relocate your business, expand to a second location, or launch your next venture while enjoying the convenience of living and working side by side on this incredible 2+ acre property. This unique

    Karen Clark Clark & Co Realty, LLC

    14236 Drapers Mill Rd, Greensboro, MD 21639
  • /21

    $319,000

    $31K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,460 Sq Ft

    1308 Chesapeake Dr, Denton, MD 21629

    Well maintained ranch style home located in Cul -de -sac backing to trees. Three bedrooms ,two full baths , Eat in Kitchen, bright Living room plus den overlooking wooded back yard. Deck is ideal for that outdoor space to entertain. Two car garage offers space for storage in addition to parking. Sellers are offering allowance for new flooring. Make this your new home!

    Bonnie Johnson Keller Williams Realty

    1308 Chesapeake Dr, Denton, MD 21629
  • /42

    $549,900

    • 4 Beds
    • 2.5 Baths
    • 2,304 Sq Ft

    3720 Payne Rd, Preston, MD 21655

    Welcome to your private countryside retreat on over 18 acres in the heart of Caroline County. This charming farmhouse-style home offers 4 bedrooms and 2.5 baths with over 2,300 sq ft of living space, combining comfort and functionality in a peaceful rural setting. The property features a mix of open land and wooded acreage, including over 6 acres in Forest Conservation, providing both privacy and

    Heather Brummell Keller Williams Realty

    3720 Payne Rd, Preston, MD 21655
  • /40

    $350,000

    $10K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,056 Sq Ft

    608 Market St, Denton, MD 21629

    Full Re-Hab 2023! Home shows well. The best of Downtown Living! This refurbished Farmhouse, has all the feels of intown country living with all the new modern ammenties! Large Eat- in Kitchen with Tons of Storage! Family Room with Fireplace, leads to a side yard Patio for entertaining! Upstairs you will find three nice size Bedrooms, 2 Full Baths, and a Loft area. Attic has finished space

    Kathleen Brenton Brenton Realty Group

    608 Market St, Denton, MD 21629
  • /11

    $269,900

    • Land
    • 14.71 Acres
    • $18,348 per Acre

    0 Trunk Rd Unit MDCM2007270, Henderson, MD 21640

    14.71± acre perc-approved parcel on Trunk Line Rd in Henderson, MD! This beautiful wooded lot offers a conventional perc approved for 4+ bedrooms and provides an excellent opportunity to build your dream home, private retreat, or future homestead. Property features approximately 466 feet of road frontage along Trunk Line Road and includes a designated sewage reserve area shown on recorded plat.

    Heather Branham The Parker Group

    0 Trunk Rd Unit MDCM2007270, Henderson, MD 21640
  • /27

    $339,000

    • 3 Beds
    • 2 Baths
    • 1,680 Sq Ft

    208 Oriole Ave, Ridgely, MD 21660

    Charming 3-bedroom, 2-bath rancher located in Ridgely! Inside, you’ll find comfortable one-level living with a functional open layout connecting the living room and kitchen, complete with stainless steel appliances. The spacious primary suite features a large en-suite bath and private doors leading directly to the backyard deck. Two additional generously sized bedrooms provide plenty of space for

    Alicia Gannon Dulin Benson & Mangold, LLC

    208 Oriole Ave, Ridgely, MD 21660
  • /6

    $360,000

    $40K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,128 Sq Ft

    26784 Bilbrough Rd, Goldsboro, MD 21636

    Welcome to your private slice of Eastern Shore living in Goldsboro. Set on 4.7 secluded acres, this 2022-built home offers the space, comfort, and modern features today’s market demands. With over 2,100 square feet, 4 bedrooms, and 2 full baths, the layout is open, bright, and designed for seamless everyday living. Step inside to a spacious floor plan that flows effortlessly from room to

    Sandra Bradley Keller Williams Select Realtors of Easton

    26784 Bilbrough Rd, Goldsboro, MD 21636
  • /41

    $399,999

    $19K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    11231 River Rd, Ridgely, MD 21660

    Looking for a nice House, Private & Lots of Land to Roam??? THIS Is IT!!!! Home features 3 Bedrooms, 2 Full Baths, Large Kitchen/Dining Combo With Lots of Storage- Updated Granite Countertops and Newer appliances. Spacious Family Room with FIreplace. Glassed in Sunroom for Entertaining! Garage with finished space for possible office with Running water & Electric. Garage also feauteres a second

    Kathleen Brenton Brenton Realty Group

    11231 River Rd, Ridgely, MD 21660
  • /54

    $445,000

    • 3 Beds
    • 2 Baths
    • 2,044 Sq Ft

    23283 Magnolia Hills Rd, Denton, MD 21629

    This charming ranch-style home in the desirable Magnolia Hill community offers a perfect blend of comfort and modern living. With 3 spacious bedrooms and 2 full bathrooms, the open floor plan with cathedral ceilings invites natural light, creating a warm and welcoming atmosphere. The eat-in kitchen features an island, ideal for casual meals, while the adjoining dining area is perfect for

    Tricia Wilson Wilson Realty & Staging LLC

    23283 Magnolia Hills Rd, Denton, MD 21629
  • /36

    $250,000

    • 2 Baths
    • 3,028 Sq Ft

    130 Halltown Rd, Marydel, MD 21649

    Can you turn this space into a home? It’s the kind of opportunity that doesn’t come around often here in Marydel. This former church turned community hall sits on just under an acre and offers over 3,000 square feet to work with, including a wide open event space and a surprisingly large kitchen at just over 515 square feet. The subflooring and joists in the main hall have already been replaced

    Micheal Vakas EXP Realty, LLC

    130 Halltown Rd, Marydel, MD 21649
  • /27

    $250,000

    • 3 Beds
    • 2 Baths
    • 1,311 Sq Ft

    25910 Fox Grape Rd, Greensboro, MD 21639

    Quiet living in Fox Grape Farms. Whether you are downsizing or just starting out, this home offers one-level living with 3 bedrooms, 2 full baths and an open living room that flows into the dining area. Situated on a 0.60 +/- parcel, the property also features two (2) storage sheds. Located approximately 7 miles from Denton, MD, 11 miles from Tuckahoe State Park and 16 miles from the Harrington

    John Fifer Brokers Realty Group, LLC

    25910 Fox Grape Rd, Greensboro, MD 21639
  • /18

    $325,000

    $25K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,302 Sq Ft

    25865 Brookwood Rd, Greensboro, MD 21639

    Sold as-is. Spacious 3 bedroom 2 full bathroom rancher located in sought-after Fox Grape neighborhood. Home is situated on private, wooded 1.23+/- acre lot. Included in the sale is an additional, adjacent .60+/- acre wooded lot for a total of 1.83+/- acres of land. Newer kitchen cabinets. Nice concrete patio, paved driveway and detached two car garage with additional workshop with power and

    Brian Petzold Benson & Mangold, LLC

    25865 Brookwood Rd, Greensboro, MD 21639
  • /11

    $269,900

    Open Sun 12PM - 3PM
    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    11 9th St, Ridgely, MD 21660

    Step into this well kept 2 bedroom, 1 bath rancher and feel instantly at home. Enjoy your morning coffee or an afternoon barbeque on the back patio with a privacy fenced back yard. Recent updates include vinyl plank flooring (2024), New roof, new refrigerator, new light fixtures and a fully encapsulated crawl space with sump pump - french drain and dehumidifier. All that's needed is your touch of

    Diane Wenk Wright Real Estate

    11 9th St, Ridgely, MD 21660
  • /2

    $301,990

    New Construction
    • 4 Beds
    • 2 Baths
    • 1,460 Sq Ft

    121 Hobbs St, Greensboro, MD 21639

    Come discover 121 Hobbs Street, a new home soon to be under construction in the quaint Kinnamon Meadows community of Greensboro, MD. The Helena is an inviting 1,460 square foot cottage-style ranch home that offers four bedrooms, two bathrooms, and a one-car garage. The long, welcoming foyer of this home allows for the three guest bedrooms and guest bathroom to be separate from the living areas of

    D.R. Horton Builder
    121 Hobbs St, Greensboro, MD 21639
  • /2

    $75,000

    • Land
    • 4.66 Acres
    • $16,094 per Acre

    412 Railroad Ave, Federalsburg, MD 21632

    LIST PRICE IS OPENING BID. Online Auction Only! Bidding begins Friday, June 5th, and ends Wednesday, June 10, 2026 at 2:00PM. Potential Commercial/Industrial Development Opportunity4.66± Acres of Undeveloped Land in Federalsburg, MD This is a prime opportunity to acquire approximately 4.66 acres of undeveloped land located within the incorporated Town of Federalsburg in Caroline County,

    Larry Cooper Alex Cooper Auctioneers, Inc.

    412 Railroad Ave, Federalsburg, MD 21632
  • /46

    $445,000

    • 4 Beds
    • 2 Baths
    • 1,986 Sq Ft

    25699 Auction Rd, Federalsburg, MD 21632

    Opportunity to purchase this remodeled residence situated on over 18 acres. Improements include new luxury vinyl plank flooring and Advantech subfloors to a fully replaced middle beam for lasting structural integrity. Nearly all windows and doors are brand new, the heating system has been upgraded to an efficient heat pump, and the electrical system now features a 200-amp panel, a dedicated

    Barbara McCaffrey Redfin Corp

    25699 Auction Rd, Federalsburg, MD 21632
  • /28

    $190,000

    • Land
    • 7.99 Acres
    • $23,780 per Acre

    Parcels #82 & #96 Drapers Mill Rd, Goldsboro, MD 21636

    Discover the possibilities with these 2 buildable lots totaling 7.994± acres on Maryland’s beautiful Eastern Shore. Each parcel is perc approved for a 4-bedroom home, offering flexibility whether you're ready to build now or planning for the future.The property is clearly marked with blue paint and stakes, making it easy to walk and envision your plans. Both lots are wooded, providing natural

    Erin Anderson Chesapeake Real Estate Associates, LLC

    Parcels #82 & #96 Drapers Mill Rd, Goldsboro, MD 21636
  • /24

    $490,000

    $8K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,720 Sq Ft

    9472 Quail Run Rd, Denton, MD 21629

    Welcome Home!! Lots of upsides on this 4 bedroom, 2.5 bath home. Harwood floors throughout, new roof in 2024, 8-mini splits for comfort and efficiency. Enjoy the summer evenings on the screened-in deck with fans and lights. Enjoy the summer days with the family making trails through the woods and dip your toes in the creek running through the back of the property. Approx. 24' x 28' work shop or

    J D Fisher Hostetter Realty

    9472 Quail Run Rd, Denton, MD 21629
  • /12

    $299,900

    • 3 Beds
    • 1 Bath
    • 1,024 Sq Ft

    5 7th St, Ridgely, MD 21660

    Don't wait to tour this wonderfully renovated home in the Greenridge community! Lots to love from top to bottom. Completely rehabbed with Hickory Vinyl Plank flooring throughout and all freshly painted. New stainless steel appliances in the spacious kitchen with center island and lots of cabinet and working space plus a full pantry. All new beautiful bathroom with rain shower head. A laundry room

    Marcia Rostien Long & Foster Real Estate, Inc.

    5 7th St, Ridgely, MD 21660
  • /31

    $319,900

    $19K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,748 Sq Ft

    10280 Log Cabin Rd, Denton, MD 21629

    The Joy of One level Living! This Rancher comes with 3 Nice size Bedrooms and 2 Full Baths. Eat-in Kitchen with Plenty of Storage. Family Room with FirePlace, Living Room, Enclosed Sunroom and a Seperate Laundry Room. Outdoors features just over 2 Acres! Large Patio for entertaining, POND, with Gazebo, Shed and a nice level lot with Mature trees. Home could use some updating but offers good bones

    Kathleen Brenton Brenton Realty Group

    10280 Log Cabin Rd, Denton, MD 21629
  • /25

    $334,900

    $5K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,440 Sq Ft

    147 Mill St, Preston, MD 21655

    Well Maintained 4 Bed 2 Full Bath Cape Cod. Large Eat-in Kitchen w/ Stainless Steel Appliances, Granite Countertops and Center Island!Nice Size Family Room. Outdoors feature a Large Shed with Heat and Air (currently used as a very nice office) , Separate Shed for storage at the back of Spacious level Lot. Patio for entertaining and more... Home is less than 1 Mile to Choptank River Landing!

    Kathleen Brenton Brenton Realty Group

    147 Mill St, Preston, MD 21655
  • /27

    $369,900

    $5K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 2,268 Sq Ft

    803 Market St, Denton, MD 21629

    This inviting Victorian offers 4 bedrooms and 1.5 baths, that’s perfect for unwinding at the end of the day. Inside, natural light fills the main level, highlighting warm hardwood floors and comfortable living spaces. The living and dining areas connect seamlessly, creating an easy flow for everyday living. The kitchen features ample cabinet and counter space, stainless steel appliances, and a

    Steven Parsons Coldwell Banker Realty

    803 Market St, Denton, MD 21629
  • /77

    $875,000

    • 4 Beds
    • 3 Baths
    • 3,149 Sq Ft

    3547 Prchal Rd, Preston, MD 21655

    Pride of ownership shines throughout this beautifully appointed home set on over 4 acres, including approximately 2.5 wooded acres with peaceful walking trails —or a great spot for hunting already equipped with a deer stand.A major renovation in 2006 nearly doubled the living space, transforming the property into a spacious 4-bedroom, 3-bathroom residence designed for both comfortable living

    Amy Endzel Keller Williams Select Realtors of Annapolis

    3547 Prchal Rd, Preston, MD 21655
  • /62

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,588 Sq Ft

    1010 S 2nd St, Denton, MD 21629

    Nestled on the edge of town, 1010 S 2nd Street delivers the convenience of in-town living without in-town taxes. Situated on 1.06 beautifully landscaped acres with mature plantings, this 3-bedroom, 2-bath home offers a spacious feel inside and out. Interior features include hardwood, LVP, and tile flooring, along with a cozy pellet stove fireplace insert for efficient heating, complemented by hot

    Roger Boyce Chesapeake Real Estate Associates, LLC

    1010 S 2nd St, Denton, MD 21629
  • /50

    $419,000

    $10K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,382 Sq Ft

    225 S 2nd St, Denton, MD 21629

    Welcome to one of Denton’s most charming historic homes — where timeless architecture, gracious living, and small-town warmth come together beautifully. Situated on a picturesque corner lot in the heart of Denton’s historic district, this lovingly maintained Victorian offers the kind of character, craftsmanship, and sense ofcommunity that is increasingly hard to find. From the moment you

    Barbara McCaffrey Redfin Corp

    225 S 2nd St, Denton, MD 21629
  • /18

    $279,900

    • 3 Beds
    • 1.5 Baths
    • 1,694 Sq Ft

    156 Main St, Preston, MD 21655

    Located in the heart of Preston, this classic 1900-built home offers a solid opportunity for both homeowners and investors alike. Inside, the home features 3 bedrooms and1.5 bathrooms and a functional layout that includes a combined laundry room, bath, and mudroom with direct access to the back deck—adding everyday practicality. The kitchen has been updated with durable luxury vinyl plank (LVP)

    Chuck Mangold Benson & Mangold, LLC

    156 Main St, Preston, MD 21655
  • /2

    $210,000

    • 3 Beds
    • 2 Baths
    • 1,484 Sq Ft

    112 Noble Ave, Preston, MD 21655

    Investor Alert! 100% occupied duplex with a 2 bedroom, 1 bath downstairs and a 1 bedroom 1 bath upstairs. Situated in the heart of Preston and close proximity to the school.

    Chuck Mangold Benson & Mangold, LLC

    112 Noble Ave, Preston, MD 21655
  • /33

    $249,900

    Open Sat 10AM - 12PM $15K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    4 N Maple Ave, Ridgely, MD 21660

    **Open House Saturday, June 6 from 10am-12pm**Step into this cozy home tucked away in a peaceful, established neighborhood. Designed for easy living, it’s an affordable, low maintenance option perfect as a starter or downsize. Inside, you’ll find fresh paint and updated flooring which creates a modern feel from the moment you enter. The living room offers a welcoming space to relax and

    Crystal Smith RE/MAX Executive

    4 N Maple Ave, Ridgely, MD 21660
  • /18

    $4,250,000

    • 3 Beds
    • 2.5 Baths

    10870 River Rd, Denton, MD 21629

    Productive Caroline County grain farm approximately 340 acres in 4 parcels with 270+/- tillable acres with 200+/- under pivot. Soil has been grid sampled and is well drained. Farm is improved with three large machine sheds, the potentially usable footprint of a pervious milking parlor and a 3 bedroom, 2.5 bath Rancher overlooking the Choptank River. No easements.

    Jim Corson Benson & Mangold, LLC

    10870 River Rd, Denton, MD 21629
  • /63

    $399,000

    $9K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,300 Sq Ft

    7392 Todds Wharf Rd, Preston, MD 21655

    This very comfortable rancher with a large high-quality above-ground pool with direct access to sunroom and into the home without getting feet dirty (yeah)! Roomy kitchen and open floor plan allows large gatherings to enjoy the roominess. Working wood-burning fireplace is great for use to heat home all winter or just on-call use when you want the ambiance. Convenient mudroom off garage with

    Agent Photo

    Bonnie Duley

    Long & Foster Real Estate, Inc.

    (667) 843-7490

    7392 Todds Wharf Rd, Preston, MD 21655
  • /12

    $575,000

    • Land
    • 61.88 Acres
    • $9,292 per Acre

    17619 Melville Rd, Henderson, MD 21640

    The Melville Rd Farm is located on the east side of Melville Road and is bordered to the north by Trunk Line Road. The property includes approximately 51± acres of tillable ground along with 11± acres of wooded areas primarily situated around drainage ditches, providing natural transitions and wildlife cover. Two transmission lines run through the center of the farm, offering access corridors and

    Benjamin Alder The Land Group

    17619 Melville Rd, Henderson, MD 21640
  • /49

    $259,900

    $65K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,448 Sq Ft

    522 Market St, Denton, MD 21629

    Investor special in the heart of Denton! This duplex at 522 Market St offers incredible potential for the right buyer looking to add value and build equity. Featuring two separate units, each level includes 2 bedrooms and 1 full bathroom, providing a functional layout ideal for rental income or multi-generational living. This also has potential to be converted back into a single family

    Mike Lee Elmore EXP Realty, LLC

    522 Market St, Denton, MD 21629
  • /36

    $430,000

    $15K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,492 Sq Ft

    1709 Cattail Commons Way, Denton, MD 21629

    Welcome to 1709 Cattail Commons Way, located in the highly desirable Savannah Overlook community in Denton, MD. This beautifully maintained 4-bedroom, 2.5-bath home offers a spacious open floor plan, modern upgrades, and move-in ready convenience—perfect for today’s buyer seeking comfort, functionality, and style. The main level features a bright and open layout ideal for both everyday living and

    Kaitlyn Collins Benson & Mangold, LLC

    1709 Cattail Commons Way, Denton, MD 21629
  • /45

    $529,900

    $100K PRICE DROP
    • Studio
    • 3,600 Sq Ft

    310 Main St, Marydel, MD 21649

    Excellent investment opportunity. Also perfect for a homeowner, live in one unit and let the other units pay your mortgage. 4-unit residential apartments fully rented with long-term tenants. Additional office space available. 5 units total. Current income from 4 units is $5,100/month, potentially $6,100/month including the office. Plenty of parking for tenants, guests, and customers. Updated

    Raphael Szendro R&R Executive Realty

    310 Main St, Marydel, MD 21649
  • /3

    $49,000

    $6K PRICE DROP
    • Land
    • 14,810 Sq Ft
    • $144,118 per Acre

    507 W Central Ave, Federalsburg, MD 21632

    Discover a unique opportunity to create your dream home on this spacious 0.34-acre parcel of land, nestled in a serene suburban setting. This property offers a blank canvas for your vision, allowing you to design a residence that perfectly suits your lifestyle and preferences. Imagine waking up each day to the gentle sounds of nature, with the peaceful ambiance of a suburban neighborhood

    Joni Barrow Coldwell Banker Realty

    507 W Central Ave, Federalsburg, MD 21632
  • /2

    $272,000

    $2K PRICE INCREASE
    • 2 Beds
    • 1 Bath
    • 864 Sq Ft

    325 Carter Ave, Denton, MD 21629

    Excellent cozy home just waiting for you in the town of Denton with the small town atmosphere and a lot of amenities. Affordably priced, close to shopping, easy commute to the Western Shore and close enough to Delaware and Maryland beaches. Come see today because this home will not last long.

    George Thompson Long & Foster Real Estate, Inc.

    325 Carter Ave, Denton, MD 21629
  • /15

    $189,000

    $26K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,406 Sq Ft

    24876 Meeting House Rd, Denton, MD 21629

    Traditional country style home sits right out side town limits. Close to town and Denton amenities, make this an excellent location for convenience. Nice size yard for a garden, pets, or children. This has been a rental for many years and has always been cared for. Continue this as a rental or make this your home. With a bit of love this could be a great starter home. Property being sold as -is,

    Kat Thompson Benson & Mangold, LLC.

    24876 Meeting House Rd, Denton, MD 21629
  • /58

    $485,000

    Coming Soon
    • 2 Beds
    • 2 Baths
    • 1,952 Sq Ft

    12397 Ridgely Rd, Ridgely, MD 21660

    Picture your horse here! Grazing in lush pastures safely fenced with Electro-Braid, training in the round pen or the 60' x 120' dressage arena, or resting in one of 4 fully matted stalls with fans in the main barn (there are two more stalls in the other stable along with hay storage.) In the main barn, two of the stalls can be joined to create a foaling stall with a monitor camera!For the

    Deborah Dawkins Coldwell Banker Realty

    12397 Ridgely Rd, Ridgely, MD 21660
  • /29

    $309,900

    $20K PRICE DROP
    • 4 Beds
    • 1.5 Baths
    • 1,350 Sq Ft

    115 Boyce Mill Rd, Greensboro, MD 21639

    Welcome to this charming, Cape-Cod with a Full Unfinished basement—perfectly nestled on a spacious 1/2 Acre! This property gives you that “welcome home” feeling the moment you arrive. Inside, you’ll find a bright and inviting living area featuring a cozy electric fireplace insert and beautiful wood‐beam accents. The freshly renovated kitchen is thoughtfully designed and opens seamlessly to the

    Kathleen Brenton Brenton Realty Group

    115 Boyce Mill Rd, Greensboro, MD 21639
  • /13

    $449,000

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,712 Sq Ft

    13926 Quail Ct, Greensboro, MD 21639

    Brand‐new construction in a peaceful country setting! Enjoy easy one‐level living in this open‐layout rancher filled with natural light. The spacious living, dining, and kitchen areas create the perfect flow for everyday living and entertaining. The huge primary suite sits privately on one side of the home, complete with a walk‐in closet and ensuite bathroom. On the opposite side, you’ll find two

    Amanda Morgan Brenton Realty Group

    13926 Quail Ct, Greensboro, MD 21639

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